title: Synthesis of oligo(α-D-glycosyl phosphate) derivatives by a phosphoramidite method via boranophosphate intermediates.
abstract: An efficient method for the synthesis of short oligo(α-D-glycosyl boranophosphate) derivatives by using an α-D-glycosyl phosphoramidite as a monomer unit was developed. The synthesis of oligomers was carried out by repeating a cycle consisting of the condensation of the monomer unit with a terminal hydroxy group of carbohydrates, boronation of the resultant phosphite intermediates, and terminal deprotection. The phosphoramidite monomer unit was synthesized from the corresponding glycosyl iodide and methyl N,N-diisopropylphosphonamidate in a highly α-selective manner. Di- and tri(α-D-glycosyl boranophosphate) derivatives obtained by the synthetic cycle were converted into the corresponding H-phosphonate diester derivatives, which were then used to synthesize di- and tri(α-D-glycosyl phosphate) derivatives including a fragment of Leishmania glycocalyx lipophosphoglycans.
authors.affiliation: Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan.
authors.forename: Shoichi
authors.initials: S
authors.lastname: Fujita
authors.forename: Natsuhisa
authors.initials: N
authors.lastname: Oka
authors.forename: Fumiko
authors.initials: F
authors.lastname: Matsumura
authors.forename: Takeshi
authors.initials: T
authors.lastname: Wada
mesh_terms: D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D001880:Boranes / Q000737:chemistry; D001895:Boron / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D019276:Glycocalyx / Q000737:chemistry; D006028:Glycosphingolipids / Q000138:chemical synthesis*; D006031:Glycosylation; D006801:Humans; D007891:Leishmania / Q000254:growth & development; D007896:Leishmaniasis / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000627:therapeutic use; D063065:Organophosphonates / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry; D017905:Phosphites / Q000737:chemistry; D058105:Polymerization
chemical_list: D000981:Antiprotozoal Agents; D001880:Boranes; D004952:Esters; D006028:Glycosphingolipids; D009844:Oligosaccharides; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D010710:Phosphates; D017905:Phosphites; C510710:boranophosphate; C008290:lipophosphonoglycan; C434331:phosphoramidite; D001895:Boron